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The Best Dresses to Wear With Knee High Boots

Knee high boots are a versatile and stylish accessory that can elevate any outfit, especially when paired with the right dress. Whether you’re looking to create a chic and polished look for a night out on the town or want to add a touch of edge to your everyday wardrobe, there are countless ways to style knee high boots with dresses. From flowy maxi dresses to sheath minis, we’ve rounded up some of the best dresses to wear with knee high boots for any occasion.

A dress and knee hight boots can be a great way to transition to spring, or the perfect choice to kick off fall. You can extend the wear of your favorite dresses into winter by adding a pair of knee high boots. Let’s explore some different styles of dresses that work especially well with tall boots. 

Sweater dresses: your go-to option for cold weather

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The perfect winter outfit is a sweater dress because it is comfortable and fashionable at the same time. Consider wearing your stylish pair of knee-high boots with a chunky knit turtleneck sweater dress during the colder months. The contrast between the shoes’ solidity and the sweater’s fluffy feel creates an appealing combo.

Pick a dress with ribs on it for a more figure-hugging look. These cute dresses are perfect for casual weekend brunches and formal office settings. Add some refinement and draw attention to your waist by accessorizing with a large belt.

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Midi Dresses: The Pinnacle of Style

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A midi dress’s appeal and modesty are perfectly balanced. Wear leather knee-high boots with a patterned midi dress for a timeless, classic style. This outfit is quite adaptable; it looks great for a romantic dinner date and everyday wear at the office. Select a midi dress with a striking print or a unique material, like silk or velvet, to give your ensemble a little edge. Your choice of prints and jacket pairings will make this stylish look more casual or more formal.

Earthy Green Midi Dress with Denim Jacket

Combine a cotton/rayon blend waist-defined midi dress with a denim jacket and tall light brown boots for an early spring outfit. The neutral hue of these boots compliments the green of the dress, and helps to lengthen the leg line.

For a more modern look, try this tie-waist denim jacket with this dress.

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Dress- Old Navy; Boots- DSW; available in wide calf; Denim Jacket- Old Navy

Floral Puff Sleeve Dress and Black Knee High Boots

The dark background of this floral print midi dress makes it perfect for black boots. The midi length makes an elegant look paired with knee boots. This combo makes another good choice for spring.

The combination of a floral dress with knee boots is perfect for transitioning between seasons. The dark background of the dress adds a touch of autumnal or winter sophistication, while the bright floral pattern adds a pop of color reminiscent of spring or summer, making it a versatile choice for transitional weather.

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Dress- Old Navy; Boots- Amazon (available in wide calf)

Maxi Dresses: Stylish and Airy Throughout the Year

Maxi dresses have a carefree grace and look stylish with knee-high boots. If you want to add some movement to your ensemble and show off your shoes when you walk, think about wearing a maxi dress with a high slit. Select a long gown with an airy floral motif and wear it with suede boots for a bohemian look. This ensemble is ideal for a laid-back day out or weekend trip.

Maxi Sweater Dress with Knee High Boots

For the perfect winter outfit, try pairing a maxi length sweater dress with knee high boots. While ankle boots are always an option, and much of the tall boots don’t show with a maxi dress, they still help create a long continous line that is elegant and stylish. Pair light colored dresses with light colored boots, and dark dresses with dark boots for a continuous lean look. Tall boots also add warmth to a winter outfit.

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Dress- Old Navy; purse- Amazon; Boots- DSW

Floral Maxi Dress with Tall Boots

For boho vibes, pair a floral maxi dress with tall boots. Pick a pair of boots with some heel to them to add some height and fight the frump that the extra fabric in a long flowy maxi can sometimes bring.

Wear this look to a winter bridal shower or for date night.

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Dress- Amazon

Mini Dresses: Stylish and Adorable

Knee-high boots with little dresses are a bold combo that looks amazing. If your dress is fitted, choose slouchy boots for a balanced effect; if your dress is flowy and loose, choose sleek fitted boots. This outfit is fascinating and stylish because of the contrast in shapes. Select a shiny or sequined minidress for a night out, or date night, and wear it with chic stiletto knee-high boots. This ensemble is not only fashionable, but it also gives off a confident, daring air. Top your mini dress with a leather jacket for a bit of edgy style. 

Baby Doll Dress with Tall Boots

Your mini dress doesn’t have to be super short. Pair a baby doll dress that hits just at the knee with tall boots for a cute and flirty look.

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Dress- option; option; Jacket- option; boots

Pinafore Mini Dress with Black Boots

Another adorable option in a mini dress is a pinafore jumper paired with a turtleneck and tall boots. This option is a soft fine corduroy. Accessorize with a headband for a youthful look.

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Dress- Amazon; Boots- Amazon; headband- option

Floral Mini Dress

A floral mini dress with a fitted option makes a great choice for pairing with tall boots. In the winter, you can add tights for warmth and modesty. Black tights would help create a continous leg lenthening line with this outfit.

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Dress- Old Navy; boots- Amazon

Shirt dresses: the ultimate casual outfit

According to the situation, shirt dresses can be styled up or down. They are incredibly versatile. Wear brown boots with a denim shirt dress for a refined yet carefree style. To define your silhouette and tighten your waist, wear a leather belt. Choose a solid-colored silk shirt dress and wear it with black knee-high boots for a more formal look. This style is classy and appropriate for many occasions.

Midi Shirt Dress with Boots

Pair a midi shirt dress with a cardigan or blazer for a work worthy look. It makes a great option for wearing tall boots to the office.

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Dress- Old Navy; cardigan- similar; boots- Amazon

Mini Flannel Shirt Dress with Boots

Tall boots are a great way to dress up a more casual plaid flannel shirt dress.

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Dress- Amazon; Boots- Amazon

The Tweed Shift Dress: An Elegant Combination

A straight shift dress makes a perfect pairing with knee high boots. Wear more casual materials with casual boots in suede and dressier dress versions with leather boots. For winter or chilly spring days, opt for a tweed shift for a little warmth.

This elegant dress could be worn for Easter Sunday, a bridal shower or even to the office.

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Dress- Amazon

Shop more dress-boots combinations:

Styling tips to look elegant

Contrasting textiles

 An eye-catching ensemble can be produced by combining contrasting textiles. Consider wearing a silky, matte wool dress with shiny patent leather boots. The variation in sheen gives your ensemble more visual appeal.

Seasonal Materials

 Use seasonal materials to elevate your look. Suede boots and a cable knit outfit can look stylish and comfortable in the fall and winter. Think about pairing smooth leather knee-high boots with a chiffon dress or lighter textures for spring.

Combining Textures

 Be bold and combine colors and textures in your footwear. A floral dress and knee-high boots made of leather can make a statement in terms of fashion.


Balancing Proportions

Take into account your outfit’s proportions when layering. An attractive, lengthened silhouette can be achieved by wearing a trench coat over a minidress and knee-high boots. Layering is a great way to adjust your wardrobe to changing weather conditions. For a sleek and elegant look in winter, a midi dress paired with light long coat is a great option.

Adding depth with style

 Layering is sometimes about something other than comfort; it can also be used to add depth. To go with your boots, wear a colorful kimono or a brightly colored scarf layered over a neutral dress. 

Accessorizing with Statement Pieces:

Bold Jewelry

 If the remainder of your ensemble is more subdued, a statement necklace or a set of huge hoop earrings can focus on your features and offer a glamorous touch.

Hats and Headgear

When worn with knee-high boots, hats look fantastic. A beanie can lend coziness and casual look to the ensemble, while a wide-brimmed felt hat might add a bohemian touch.

Purses & Bags

Pick a bag that goes well with your boots. While a velvet handbag would look good with suede boots, a leather pouch goes excellent with leather boots.

Putting on Knee-High Boots with Confidence

Try combining different textures to elevate your knee-high boot combination. For example, try wearing a ribbed dress with elegant leather boots. For extra flair, layer well with coats or scarves. Make a statement with striking accessories like a statement necklace or a sophisticated hat. The most crucial component is confidence; wear your clothes and boots with comfort and grace to make them statements of elegance and sense of style rather than just a simple trend statement.

Wrapping up

Knee-high boots are an elegant and functional addition to any outfit. These styling suggestions and the appropriate outfits can help you create various appearances that complement your style and the event. Knee-high boots are the ideal footwear to match every dress outfit, whether you’re trying for a casual, stylish, or loud look. Keep in mind that the whole point of fashion is self-expression, so don’t be scared to play around and enjoy your sense of style!

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